Process for the mass coloration of thermoplastics with anthraquinonylaminotraizines

ABSTRACT

A process for the mass coloration of thermoplastics with anthraquinonylaminotriazines of the formula ##STR1## wherein each of X 1  and X 2  is an alkylmercapto or arylmercapto group or a group of the formula --NR 1  R 2 , in which each of R 1  and R 2  is alkyl, cycloalkyl, aralkyl or aryl, and R 2  can additionally be hydrogen, or R 1  and R 2  together with the nitrogen atom to which they are attached and optionally a further heteroatom form a 5- or 6-membered ring, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR2## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1. Yellow to orange colored fibres of clear shade, good color strength and fastness properties are obtained.

The present invention relates to a process for the mass colouration of thermoplastics with anthraquinonylaminotriazines of the formula ##STR3## wherein each of X₁ and X₂ is an alkylmercapto or arylmercapto group or a group of the formula --NR₁ R₂, in which each of R₁ and R₂ is alkyl, cycloalkyl, aralkyl or aryl, and R₂ can additionally be hydrogen, or R₁ and R₂ together with the nitrogen atom to which they are attached and optionally a further heteroatom form a 5- or 6-membered ring, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR4## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1.

Alkylmercapto groups represented by X₁ and X₂ in formula (1) are preferably those containing 1 to 6 carbon atoms. Suitable arylmercapto groups are e.g. naphthylmercapto groups and, in particular, phenylmercapto groups which are unsubstituted or substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms. Where X₁ and X₂ are groups of the formula --NR₁ R₂, the preferred meanings of R₁ and R₂ are alkyl groups of 1 to 20 carbon atoms, alkoxyalkyl groups, cycloalkyl groups of 5 to 10 carbon atoms, benzyl or phenylethyl groups, or phenyl groups which are unsubstituted or substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms, while R₂ can additionally be hydrogen.

The two radicals R₁ and R₂ together with the nitrogen atom to which they are attached can also form e.g. a piperidine or morpholine ring.

An arylmercapto group Y is preferably a phenylmercapto group which can be substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms. Y can also be an alkanoylamino group of 2 to 6 carbon atoms or a benzoylamino group which is unsubstituted or substituted by chlorine atoms or alkyl or alkoxy atoms of 1 to 6 carbon atoms, but is in particular a hydrogen atom or a OH group. n is preferably 0.

The anthraquinonylaminotriazine compounds to be used in accordance with the invention are known compounds. They are advantageously obtained by condensation of a chlorotriazine of the formula ##STR5## with the corresponding aminoanthraquinone, for example 1-aminoanthraquinone, 1-aminoanthraquinone-3-, -4-, -5-, -6- or -7-chloroanthraquinone, 1-aminoanthraquinone-4-hydroxyanthraquinone, 1-aminoanthraquinone-4-, -5- or -8-phenylmercaptoanthraquinone, 1-aminoanthraquinone-4- or -5-acetylaminoanthraquinone, 1-aminoanthraquinone-4- or -5-benzoylaminoanthraquinone.

The triazines of the formula (2) are obtained by the stepwise replacement of two chlorine atoms in cyanuric chloride by the amines or mercaptans X₁ H and X₂ H.

The following amines are cited as examples: methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, n-hexylamine, n-octylamine, n-decylamine, n-dodecylamine, n-hexadecylamine, or n-octadecylamine, dimethylamine, diethylamine, di-n-propylamine or di-n-butylamine, β-methoxyethylamine, γ-methoxy-n-propylamine or γ-isopropoxy-n-propylamine, cyclohexylamine, dicyclohexylamine, benzylamine, phenylethylamine, aniline, o-, m- or p-toluidine, N-methylaniline, N-ethylaniline or N-n-butylaniline, 1-aminonaphthalene, piperidine or morpholine.

Table I lists a number of anthraquinonylaminotriazines of the formula ##STR6## wherein A is the 1-anthraquinonyl radical, m is 1, and the meanings of X₁ and X₂ are indicated in columns II and III.

                  TABLE I                                                          ______________________________________                                         No.    X.sub.1           X.sub.2                                               ______________________________________                                         1    β-methoxyethylamino                                                                         β-methoxyethylamino                                2    γ-methoxypropylamino                                                                       γ-methoxypropylamino                              3    γ-isopropoxypropylamino                                                                    γ-isopropoxypropylamino                           4    benzylamino       benzylamino                                             5    phenylethylamino  phenylethylamino                                        6    n-hexadecylamino  n-hexadecylamino                                        7    n-octadecylamino  n-octadecylamino                                        8    methylamino       ethylamino                                              9    methylamino       n-butylamino                                            10   methylamino       n-hexadecylamino                                        11   ethylamino        n-octadecylamino                                        12   methylamino       dimethylamino                                           13   methylamino       diethylamino                                            14   methylamino       di-n-propylamino                                        15   methylamino       di-n-butylamino                                         16   ethylamino        dimethylamino                                           17   methylamino       anilino                                                 18   ethylamino        anilino                                                 19   isopropylamino    anilino                                                 20   n-butylamino      anilino                                                 21   n-hexadecylamino  anilino                                                 22   n-octadecylamino  anilino                                                 23   methylamino       N-methyl-anilino                                        24   ethylamino        N-methyl-anilino                                        25   dimethylamino     diethylamino                                            26   dimethylamino     diisopropylamino                                        27   dimethylamino     di-n-butylamino                                         28   dimethylamino     N-methyl-anilino                                        29   di-isopropylamino N-methyl-anilino                                        30   di-n-butylamino   N-methyl-anilino                                        31   anilino           N-methyl-anilino                                        32   N-methyl-anilino  N-ethyl-anilino                                         34   ethylmercapto     methylmercapto                                          35   ethylmercapto     n-propylmercapto                                        36   ethylmercapto     n-butylmercapto                                         37   ethylmercapto     n-hexadecylmercapto                                     38   ethylmercapto     n-octadecylmercapto                                     39   methylmercapto    phenylmercapto                                          40   ethylmercapto     phenylmercapto                                          41   anilino           phenylmercapto                                          42   N-methylanilino   phenylmercapto                                          43   N-ethylanilino    phenylmercapto                                          44   methylamino       methylmercapto                                          45   methylamino       ethylmercapto                                           46   methylamino       n-propylmercapto                                        47   methylamino       n-butylmercapto                                         48   methylamino       n-hexadecylmercapto                                     49   methylamino       n-octadecylmercapto                                     50   ethylamino        methylmercapto                                          51   diethylamino      methylmercapto                                          52   dimethylamino     methylmercapto                                          53   dimethylamino     ethylmercapto                                           54   diethylamino      ethylmercapto                                           55   di-n-butylamino   ethylmercapto                                           56   dimethyamino      n-propylmercapto                                        57   anilino           methylmercapto                                          58   anilino           ethylmercapto                                           59   anilino           n-propylmercapto                                        60   anilino           n-butylmercapto                                         61   anilino           n-hexadecylmercapto                                     62   anilino           n-octadecylmercapto                                     63   N-methylanilino   methylmercapto                                          64   N-ethylanilino    methylmercapto                                          ______________________________________                                    

Table II lists further anthraquinonylaminotriazines of the formula (3), wherein m is 2, A is the anthraquinone radical which is bonded to the triazinylamino groups in the positions indicated in column II, and X₁ and X₂ have the meanings given in columns III and IV.

                  TABLE II                                                         ______________________________________                                              Posi-                                                                     No.  tion     X.sub.1         X.sub.2                                          ______________________________________                                         65   1,4    β-methoxyethylamino                                                                       β-methoxyethylamino                           66   1,5    β-methoxyethylamino                                                                       β-methoxyethylamino                           67   1,4    γ-methoxypropylamino                                                                     γ-methoxypropylamino                         68   1,5    γ-methoxypropylamino                                                                     γ-methoxypropylamino                         69   1,4    γ-isopropoxypropyl-                                                                      γ-isopropxypropylamino                                   amino                                                              70   1,5    γ-isopropoxypropyl-                                                                      γ-isopropxypropylamino                                   amino                                                              71   1,4    benzylamino     benzylamino                                        72   1,5    benzylamino     benzylamino                                        73   1,4    n-hexadecylamino                                                                               n-hexadecylamino                                   74   1,5    n-hexadecylamino                                                                               n-hexadecylamino                                   75   1,4    methylamino     methylamino                                        76   1,5    methylamino     methylamino                                        77   1,4    butylamino      butylamino                                         78   1,5    butylamino      butylamino                                         79   1,4    dimethylamino   dimethylamino                                      80   1,5    dimethylamino   dimethylamino                                      81   1,4    morpholyl       morpholyl                                          82   1,5    morpholyl       morpholyl                                          83   1,4    anilino         anilino                                            84   1,5    anilino         anilino                                            85   1,4    phenylmercapto  phenylmercapto                                     86   1,5    phenylmercapto  phenylmercapto                                     87   1,4    n-butylmercapto n-butylmercapto                                    88   1,5    n-butylmercapto n-butylmercapto                                    89   1,4    n-hexadecylmercapto                                                                            n-hexadecylmercapto                                90   1,5    n-hexadecylmercapto                                                                            n-octadecylmercapto                                91   1,4    n-octadecylmercapto                                                                            n-octadecylmercapto                                92   1,5    n-octadecylmercapto                                                                            n-octadecylmercapto                                93   1,4    methylamino     anilino                                            94   1,5    methylamino     anilino                                            95   1,4    methylamino     N-methylanilino                                    96   1,5    methylamino     N-methylanilino                                    97   1,4    dimethylamino   anilino                                            98   1,5    dimethylamino   anilino                                            99   1,4    methylmercapto  anilino                                            100  1,5    methylmercapto  anilino                                            101  1,4    methylmercapto  N-methylanilino                                    102  1,5    methylmercapto  N-methylanilino                                    103  1,4    n-butylmercapto anilino                                            104  1,5    n-butylmercapto anilino                                            105  1,4    n-octadecylmercapto                                                                            anilino                                            106  1,5    n-octadecylmercapto                                                                            anilino                                            107  1,4    methylmercapto  phenylmercapto                                     108  1,5    methylmercapto  phenylmercapto                                     109  1,4    n-butylmercapto phenylmercapto                                     110  1,5    n-butylmercapto phenylmercapto                                     111  1,4    methylmercapto  n-hexadecylmercapto                                112  1,5    methylmercapto  n-hexadecylmercapto                                113  1,4    methylamino     dimethylamino                                      114  1,5    methylamino     dimethylamino                                      115  1,4    methylmercapto  morpholinyl                                        116  1,5    methylmercapto  morpholinyl                                        117  1,4    n-hexadecylamino                                                                               anilino                                            118  1,5    n-hexadecylamino                                                                               anilino                                            119  1,4    isopropylamino  anilino                                            120  1,5    isopropylamino  anilino                                            121  1,4    anilino         N-methylanilino                                    122  1,5    anilino         N-methylanilino                                    123  1,4    methylamino     methylmercapto                                     124  1,5    methylamino     methylmercapto                                     125  1,4    dimethylamino   methylamino                                        126  1,5    dimetylamino    methylamino                                        127  1,4    dimethylamino   methylmercapto                                     128  1,5    dimethylamino   methylmercapto                                     129  1,5    ethylamino      butylamino                                         ______________________________________                                    

Table III lists compounds of the formula ##STR7## wherein X₁ and X₂ have the meanings given in columns II and III and Y is as defined in column IV. Column V indicates the position of Y.

                  TABLE III                                                        ______________________________________                                         No.   X.sub.1    X.sub.2    Y         Position                                 ______________________________________                                         130  ethylamino butylamino hydroxy    4                                        131  cyclohexyl-                                                                               cyclohexyl-                                                                               hydroxy    4                                             amino      amino                                                          132  dimethyl-  dimethyl-  2,4-bisanilino-                                                                           4                                             amino      amino      triazinyl-6-                                                                   amino                                               133  N-methyl-  phenylamino                                                                               2,4-bisethyl-                                                                             4                                             anilino               aminotriazinyl-                                                                6-amino                                             134  N-methyl-  phenylamino                                                                               2,4-bisethyl-                                                                             5                                             anilino               aminotriazinyl-                                                                6-amino                                             135  N-methyl-  phenylamino                                                                               2,4-bisphenyl-                                                                            4                                             anilino               mercapto-tria-                                                                 zinyl-6-amino                                       ______________________________________                                    

It is also possible to use mixtures of different dyes.

Examples of thermoplastics are polyolefins, such as polyethylene, polypropylene or polyisobutylene, also polyvinyl chloride, polystyrene, as well as copolymers of styrene, such as ABS, and especially linear polyesters.

Suitable linear polyesters are in particular those which are obtained by polycondensation of terephthalic acid or an ester thereof with a glycol of the formula HO--(CH₂)_(n) --OH, in which n is an integer from 2 to 10, or with 1,4-di(hydroxymethyl)cyclohexane, or by polycondensation of a glycol ether of a hydroxybenzoic acid, for example p-(β-hydroxyethoxy)-benzoic acid. The term "linear polyesters" also comprises copolyesters which are obtained by partial replacement of terephthalic acid by another dicarboxylic acid or by a hydroxycarboxylic acid and/or by partial replacement of the glycol by another diol. However the preferred linear polyester are polyethylene terephthalates.

Colouration is effected by the conventional methods, for example by mixing the colourants with the plastics material in granulate or particulate form and extruding the mixture to fibres, sheets or granules. These latter can then be moulded to objects by injection moulding.

The colouration obtained, especially in polyester, are distinguished by good fastness to light, washing, dry cleaning, cross-dyeing, thermofixation, bleeding and chlorite bleaching, as well as by clear shades and good colour strength.

Russian Pat. No. 192.993 and German Auslegeschrift No. 1 644 532 describe anthraquinone dyes which in the 4-position contain an arylamino group. In contradistinction thereto, the colourants employed in the present invention colour polyester in shades of distinctly better fastness to light and resistance to atmospheric influences.

The invention is illustrated by the following Examples, in which parts and percentages are by weight.

EXAMPLE 1

A non-delustred polyethylene terephthalate granulate suitable for fibre manufacture is shaken in a closed vessel for 15 minutes on a mechanical shaker together with 1% of 1-(2',4'-bis-N-methyl-N-phenylamino-1',3',5'-triazinyl-6')-aminoanthraquinone. The uniformly coloured granules are then spun in a melt spinning machine (285° C.±3° C., sojourn time in the spinning machine about 5 minutes) to filaments, which are stretched and wound on a draw twister. The solubility of the colourant in polyethylene terephthalate results in a strong yellow colouration which is distinguished by outstanding light-fastness, excellent fastness to washing, dry cleaning, cross-dyeing, sublimation and rubbing after thermofixation, and also by excellent resistance to chlorite bleaching and good viscosity values.

EXAMPLE 2

1000 parts of polyethylene terephthalate granules, 10 parts of titanium oxide (Kronos RN 40) and 1 part of finely divided 1-(2',4'-bis-N-methyl-N-phenylamino-1',3',5'-triazinyl-6')-amino-4-hydroxyanthraquinone are mixed in a closed vessel for 2 hours on a roller gear table. The coloured granules are extruded at about 260° C. to strands of 2 mm, which are re-granulated. The resultant granules are processed at 270°-280° C. in a screw injection moulding machine to mouldings. The red coloration obtained is of very good light-fastness.

EXAMPLES 3-42

Table IV lists further colourants of the formula (3) which were used for colouring polyethylene terephthalate by the methods described in Examples 1 and 2. A is the anthraquinonyl radical. The meanings of X₁, X₂ and m are indicated in columns II, III and IV respectively. The position of the triazinylamino group in the anthraquinone radical is indicated in column V.

                  TABLE IV                                                         ______________________________________                                         Exam-                             Posi-                                        ple    X.sub.1     X.sub.2    m   tion  Colour                                 ______________________________________                                         3     methylamino methylamino 1   1     yellow                                 4     methylamino methylamino 2   1,5   yellowish                                                                      orange                                 5     ethylamino  ethylamino  1   1     yellow                                 6     ethylamino  ethylamino  2   1,5   yellowish                                                                      orange                                 7     n-butylamino                                                                               n-butylamino                                                                               1   1     yellow                                 8     dimethylamino                                                                              dimethylamino                                                                              1   1     yellow                                 9     diethylamino                                                                               diethylamino                                                                               1   1     yellow                                 10    diisopropyl-                                                                               diisopropyl-                                                                               1   1     yellow                                       amino       amino                                                        11    di-n-butyl- di-n-butyl  1   1     yellow                                       amino       amino                                                        12    piperidyl   piperidyl   1   1     yellow                                 13    morpholyl   morpholyl   1   1     yellow                                 14    anilino     anilino     1   1     yellow                                 15    N-methylani-                                                                               N-methylani-                                                                               1   1     yellow                                       lino        lino                                                         16    N-methylani-                                                                               N-methylani-                                                                               2   1,4   violet                                       lino        lino                                                         17    N-methylani-                                                                               N-methylani-                                                                               2   1,5   reddish                                      lino        lino                  yellow                                 18    diphenylamino                                                                              diphenylamino                                                                              1   1     yellow                                 19    phenylmercapto                                                                             phenylmercapto                                                                             1   1     yellow                                 20    methoxypropio-                                                                             methoxypropio-                                                                             1   1     yellow                                       nylamino    nylamino                                                     21    isopropoxy- isopropoxy- 1   1     yellow                                       propylamino propylamino                                                  22    methoxyethyl-                                                                              methoxyethyl-                                                                              1   1     yellow                                       amino       amino                                                        23    amino       amino       1   1     yellow                                 24    benzylamino benzylamino     1     yellow                                 25    phenylethyl-                                                                               phenylethyl-                                                                               1   1     yellow                                       amino       amino                                                        26    diisopropyl-                                                                               diisopropyl-                                                                               2   1,5   orange                                       amino       amino                                                        27    diisopropyl-                                                                               phenylmercapto                                                                             1   1     yellow                                       amino                                                                    28    diisopropyl-                                                                               p-toluidino 1   1     yellow                                       amino                                                                    29    dimethylamino                                                                              methylmer-  1   1     yellow                                                   capto                                                        30    methylmer-  methylmer-  1   1     yellow                                       capto       capto                                                        31    methylmer-  butyl-2-mer-                                                                               1   1     yellow                                       capto       capto                                                        32    methylmer-  methylmer-  2   1,5   reddish                                      capto       capto                 yellow                                 33    N-methyl-   N-methyl-   2   1,8   reddish                                      anilino     anilino               yellow                                 34    methylmercapto                                                                             anilino     1   1     yellow                                 35    methylmercapto                                                                             phenylmercapto                                                                             1   1     greenish                                                                       yellow                                 36    methylmercapto                                                                             o-phenetidino                                                                              1   1     greenish                                                                       yellow                                 37    methylmercapto                                                                             p-phenetidino                                                                              1   1     yellow                                 38    methylmercapto                                                                             4-chlorophenyl-                                                                            1   1     yellow                                                   mercapto                                                     39    methylmercapto                                                                             2,5-dichlor-                                                                               1   1     yellow                                                   phenyl                                                       40    methylmercapto                                                                             4-methylphenyl                                                                             1   1     yellow                                 41    phenylmercapto                                                                             morpholino  1   1     yellow                                 42    phenylmercapto                                                                             cyclohexyl-1-                                                                              1   1     yellow                                                   amino                                                        ______________________________________                                    

EXAMPLES 43-82

Table IV lists further colourants of the formula (4) which were used to colour polyethylene terephthalate by the methods described in Examples 1 and 2. A is the anthraquinonyl radical. The meanings of X₁, X₂ and Y are given in columns II, III and IV respectively. Column V indicates the position of Y in the anthraquinonyl radical and column VI the shade of the coloured polyester fibres.

                  TABLE V                                                          ______________________________________                                         Ex-                                 Po-                                        am-                                 si-                                        ple   X.sub.1    X.sub.2    Y       tion Colour                                ______________________________________                                         43   ethylamino ethylamino hydroxy  4    red                                   44   ethylamino ethylamino benzoyl- 5    reddish                                                          amino         yellow                                45   anilino    anilino    hydroxy  4    red                                   46   N-methyl-  N-methyl-  hydroxy  4    red                                        anilino    anilino                                                        47   N-methyl-  N-methyl-  benzoyl- 5    reddish                                    anilino    anilino    amino         yellow                                48   N-methyl-  N-methyl-  benzoyl- 5    reddish                                    anilino    anilino    amino         yellow                                49   N-methyl-  N-methyl-  phenylmer-                                                                              4    red                                        anilino    anilino    capto                                               50   N-methyl-  N-methyl-  phenylmer-                                                                              5    yellow                                     anilino    anilino    capto                                               51   butylamino butylamino benzoyl- 4    red                                                              amino                                               52   cyclohexyl-                                                                               cyclohexyl-                                                                               benzoyl- 4    claret                                     amino      amino      amino                                               53   diethyl-   diethyl-   benzoyl- 4    red                                        amino      amino      amino                                               54   diisopro-  diisopro-  hydroxy  4    red                                        pylamino   pylamino                                                       55   methylmer- methylmer- 4-chlorben-                                                                             4    red                                        capto      capto      zoylamino                                           56   methylmer- butyl-2-   4-chlorben-                                                                             4    red                                        capto      mercapto   zoylamino                                           57   methylmer- dimethyl-  phenylmer-                                                                              5    yellow                                     capto      amino      capto                                               58   methylamino                                                                               methylamino                                                                               phenylmer-                                                                              5    brown-                                                           capto         ish                                                                            yellow                                59   N-methyl-  N-methyl-  phenylmer-                                                                              5    yellow                                     anilino    anilino    mercapto                                            60   N-methyl-  N-methyl-  4-chlorphe-                                                                             5    yellow                                     anilino    anilino    nylmercapto                                         61   N-methyl-  N-methyl-  phenylmer-                                                                              8    yellow                                     anilino    anilino    capto                                               62   methylmer- anilino    chlorine 3    green-                                     capto                               ish                                                                            yellow                                63   methylmer- 2-chlor-   chlorine 3    green-                                     capto      anilino                  ish                                                                            yellow                                64   methylmer- 3-chlor-   chlorine 3    green-                                     capto      anilino                  ish                                                                            yellow                                65   methylmer- anilino    chlorine 4    yellow                                     capto                                                                     66   methylmer- o-anisidino                                                                               chlorine 4    yellow                                     capto                                                                     67   methylmer- p-anisidino                                                                               chlorine 4    yellow                                     capto                                                                     68   methylmer- anilino    chlorine 6    yellow                                     capto                                                                     69   methylmer- o-toluidino                                                                               chlorine 5    yellow                                     capto                                                                     70   p-toluidino                                                                               p-toluidino                                                                               chlorine 5    yellow                                71   methylmer- anilino    chlorine 6(7) yellow                                     capto                                                                     72   methylmer- p-chlorani-                                                                               chlorine 6(7) yellow                                     capto      lino                                                           73   methylmer- m-toluidino                                                                               chlorine 6(7) yellow                                     capto                                                                     74   dimethyl-  dimethyl-  2-chloro-                                                                               4    red                                        amino      amino      benzoyl-                                                                       amino                                               75   dimethyl-  dimethyl-  3-chloro-                                                                               4    claret                                     amino      amino      benzoyl-                                                                       amino                                               76   dimethyl-  dimethyl-  2-fluoro-                                                                               4    claret                                     amino      amino      benzoyl-                                                                       amino                                               77   dimethyl-  dimethyl-  acetyl-  4    claret                                     amino      amino      amino                                               78   methylmer- phenylmer- hydroxy  4    red                                        capto      capto                                                          79   methylmer- phenylmer- benzoyl- 4    red                                        capto      capto      amino                                               80   methylmer- phenylmer- benzoyl- 5    yellow                                     capto      capto      amino                                               81   phenylmer- cyclohe-   hydroxy  4    red                                        capto      xylamino                                                       82   phenylmer- morpholino hydroxy  4    red                                        capto                                                                     ______________________________________                                     

What is claimed is:
 1. A process for the mass coloration of a thermoplastic in the melt in which the coloration is effected byincorporating in said thermoplastic in the melt an effective amount of an anthraquinonylaminotriazine of the formula (1) ##STR8## wherein each of X₁ and X₂ is an alkylmercapto or arylmercapto group or a group of the formula --NR₁ R₂, in which each of R₁ and R₂ is alkyl, cycloalkyl, aralkyl or aryl, and R₂ can additionally be hydrogen, or R₁ and R₂ together with the nitrogen atom to which they are attached form a 5- or 6-membered ring or are morpholino, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR9## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or
 1. 2. A process according to claim 1, where in the compound of the formula (1), each of X₁ and X₂ is a group of the formula --NR₁ R₂, in which R₁ and R₂ are alkyl groups of 1 to 20 carbon atoms, alkoxyalkyl groups, cycloalkyl groups of 5 to 6 carbon atoms, benzyl or phenylethyl groups or phenyl groups which are unsubstituted or substituted by chlorine atoms, alkyl or alkoxy groups, each of 1 to 6 carbon atoms, and R₂ can additionally be hydrogen.
 3. A process according to claim 1, where in the compound of the formula (1), X₁ is an alkylmercapto group of 1 to 6 carbon atoms or a group of the formula --NR₁ R₂, in which R₁ and R₂ are as defined in claim 2 and X₂ is an alkylmercapto group of 1 to 6 carbon atoms.
 4. A process according to claim 1, where the compound of the formula (1) is ##STR10##
 5. A process according to claim 1, where the compound of the formula (1) is ##STR11##
 6. A process according to claim 1, where the compound of the formula (1) is ##STR12##
 7. A process according to claim 1, where the compound of the formula (1) is ##STR13##
 8. A process according to claim 1, where the compound of the formula (1) is ##STR14##
 9. A thermoplastic mass colored by the process according to claim
 1. 10. A linear polyester mass colored by the process according to claim
 1. 